Sodium Azide → HCID 23036246, compound

HRID 1194736Notes

Reaction equation

HRID 1194736 reaction equation
[Cl:1][C:2]([C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([C:14]([Cl:18])=[C:15]([Cl:17])[Cl:16])[CH:13]=1)[CH2:9]Br)=[C:3]([Cl:5])[Cl:4].[N-:19]=[N+:20]=[N-:21].[Na+]>C(O)C>[Cl:1][C:2]([C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([C:14]([Cl:18])=[C:15]([Cl:17])[Cl:16])[CH:13]=1)[CH2:9][N:19]=[N+:20]=[N-:21])=[C:3]([Cl:5])[Cl:4]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 23036220HCID 23036220, compound

Product 1

HCID 23036246HCID 23036246, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of crude 3,5-di(trichlorovinyl)benzyl bromide (7.9 g) and sodium azide (1.9 g) in 200 ml of ethanol was heated at reflux for 1.5 hours. The reaction mixture was concentrated and the residue partitioned between 100 ml of ether and 100 ml of water. The layers were separated and the aqueous phase further extracted with ether. The ethereal layers were washed with water, dried with MgSO4, and concentrated to give 7.03 g of an oil. This material was chromatographed on silica gel (hexane then 90:10 hexane:CH2Cl2) to give 3.52 g of pure azide.

Workup

  1. temperatureat reflux for 1.5 hours
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue partitioned between 100 ml of ether and 100 ml of water
  4. customThe layers were separated
  5. extractionthe aqueous phase further extracted with ether
  6. washThe ethereal layers were washed with water
  7. dry with materialdried with MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-53305abb7afe44f98a5978f8ef061184
Source dataset
uspto-grants-1989_03
Patent number
US04816469

Reaction notes

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